EP0281112B1 - Dispositif pour effecteur une réaction hétérogène - Google Patents
Dispositif pour effecteur une réaction hétérogène Download PDFInfo
- Publication number
- EP0281112B1 EP0281112B1 EP88103194A EP88103194A EP0281112B1 EP 0281112 B1 EP0281112 B1 EP 0281112B1 EP 88103194 A EP88103194 A EP 88103194A EP 88103194 A EP88103194 A EP 88103194A EP 0281112 B1 EP0281112 B1 EP 0281112B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- capillary
- chamber
- flow
- reagent
- carrier
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01L—CHEMICAL OR PHYSICAL LABORATORY APPARATUS FOR GENERAL USE
- B01L3/00—Containers or dishes for laboratory use, e.g. laboratory glassware; Droppers
- B01L3/50—Containers for the purpose of retaining a material to be analysed, e.g. test tubes
- B01L3/502—Containers for the purpose of retaining a material to be analysed, e.g. test tubes with fluid transport, e.g. in multi-compartment structures
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/54366—Apparatus specially adapted for solid-phase testing
Definitions
- the invention relates to a device for carrying out a heterogeneous reaction for determining a component of a sample liquid on a first capillary-active carrier (T1) located in a measuring chamber (Me), to which at least one non-soluble reagent adheres.
- T1 first capillary-active carrier
- Me measuring chamber
- the invention also relates to a static one-way capillary flow valve for the device called Owen
- the object of the invention is to provide a device of this type, by means of which a heterogeneous reaction for the detection of a component of a sample liquid (analyte) can be reliably carried out solely by using the force of gravity - if necessary by rotating the device in different positions.
- Heterogeneous reactions for the detection of analytes, reactions between an analyte, at least one soluble and at least one insoluble reagent, one or more reactions taking place, can generally not be carried out in one step.
- excess sample material or reagent for example, must be removed (washing step), auxiliary reagent added and / or after a reaction (incubation step) another reagent, for example an indicator reagent, must be added.
- a device according to the invention should in particular be able to be designed as a disposable device for carrying out tests (in particular pregnancy tests). It should be able to be mass-produced and not require any individual intervention.
- the basic solution to this problem is the present device, which is characterized in that at least one soluble reagent is in a first antechamber (V1) on a second capillary-active carrier (T2) which is in capillary contact with the capillary-active carrier (T1) in the measuring chamber (Me). is located, which is connected via a first capillary (K1) to a first feed chamber (A1) to be filled from the outside through a filling opening (F1), and that the measuring chamber (Me) is also connected by a capillary arrangement (KA) which is only accessible from one under a predetermined gravitational liquid can flow through in the measuring chamber (Me), is connected to a waste chamber (Abf).
- the static capillary flow one-way valve is characterized by a chamber (2) in which an inflow capillary (4) and an outflow capillary ( 6) open, the wall surfaces (8) of the inflow capillary (4) with the wall surfaces (10, 12, 14, 16) of the chamber (2) adjoining them Include angles ( ⁇ ) which are coarser in their mean than those in their mean (ß) which cover the wall surfaces (18) of the outflow capillary (6) with the wall surfaces (20, 22, 24) of the chamber (2 ) lock in.
- the reactants in the sense of the present invention are the analyte, at least one soluble reagent and at least one insoluble reagent.
- Such reagents are familiar to the person skilled in the art and do not require any detailed explanation.
- the device is particularly suitable for carrying out enzymatic and / or immunological determination reactions, in particular using enzymes, substrates, antibodies, antigens, haptens, color-forming reagents and auxiliary reagents, such as buffers or surfactants (e.g. for detaching the analyte from serum components).
- the device is used to carry out immunological determination methods, such as competitive, simple sandwich or DASP sandwich tests.
- immunological determination methods such as competitive, simple sandwich or DASP sandwich tests.
- Such methods are for example in laboratory techniques in Biochem. and Molec. Biol., Ed. RH Burdon, PH v. Knippenberg, Elsevier, Amsterdam, Vol. 15 (1985), pp. 9-37 and Lig. Rev. 3/3 (1981) pp. 6-13.
- the analyte is bound directly or indirectly to the insoluble reagent.
- a detection reaction e.g. color formation
- a heterogeneous reaction for determining a component of a sample liquid (analyte) on a first capillary-active carrier T1 located in a measuring chamber Me, to which at least one non-soluble reagent adheres.
- At least one soluble reagent is located on a second capillary-active carrier T2 which is in capillary contact with the capillary-active carrier T1 in the measuring chamber Me in a first antechamber V1.
- “Capillary contact” means that the capillary-active carriers T1 and T2 are in capillary contact, so that the capillary-active carrier T1 can absorb liquid from the capillaries of the capillary-active carrier T2 into its capillaries.
- the pre-chamber V1 is connected via a first capillary K1 to a first feed chamber A1 to be filled from the outside through a filling opening F1 - which is the only feed chamber in the embodiment according to FIG. 1.
- the measuring chamber Me is moreover connected to a waste chamber Abf by a capillary arrangement KA, which can only flow through from the direction of the measuring chamber Me from a liquid under a predetermined gravitational force.
- the capillary arrangement KA forms an inlet of the waste chamber Abf.
- the waste chamber Abf is provided with a ventilation opening L1.
- the capillary K1 - which also applies to the capillary to be described below - has a hydraulic diameter of 0.05 mm to 2 mm, preferably a hydrodynamic diameter of 0.2 mm to 0.6 mm.
- the "hydraulic diameter” is defined as four times the quotient of the cross-sectional area and circumference of the capillary, which also describes capillaries with a non-circular cross-section which are suitable here).
- Suitable capillary-active carriers T1, T2 - which also applies to the capillary-active carriers to be described below - are paper, nonwoven, woven, knitted or porous membrane material.
- the capillary active carriers can be characterized by their suction capacity and their suction power.
- the suction height with which they suck in a liquid in a given time 300 s can be used.
- the suction height is the height of the front of the aspirated liquid above the level of the free liquid into which the capillary-active carrier is immersed.
- the initial suction speed can also be important, such as the time it takes to reach a suction height of 30 mm. In individual cases, air permeability can also be important.
- Capillary-active carriers of this type are described, for example, in DE 35 43 749.
- the chambers A1, V1, Me and Abf, the capillary K1 and the capillary arrangement KA are - which also applies to the chambers, capillaries, capillary arrangements and capillary flow one-way valves to be described below - incorporated in a flat surface of a first plate P1, which by a flat surface of a second plate P2 is covered.
- At least one of the plates P1, P2 is transparent at least in the area of the measuring chamber Me, so that one can carry out the required measurement or observation of the heterogeneous reaction.
- Glass or plastic has proven to be particularly suitable as the material for the plates P1 and P2, and polyacrylate or polystyrene as the plastic.
- a soluble reagent on the carrier T2 When using the device according to FIG. 1, there is a soluble reagent on the carrier T2 and an insoluble reagent on the carrier T1.
- a predetermined amount of a sample liquid is first placed in the feed chamber A1. This liquid releases reagent from the carrier T2 and flows with it to the carrier T1.
- a predetermined amount of a diluent (a washing and elution solution) is added to the feed chamber A1, which essentially frees the reagent T2 from the reagent and transfers the reagent to the carrier T1. Excess liquid passes through the capillary arrangement KA into the waste chamber Abf.
- the waste chamber contains either unused fleece or fleece, which is impregnated with reagents, which, if necessary, also suppress ongoing and undesired detection reactions (such as color formation or luminescence).
- the capillary K1 ensures that there is an even, gradual distribution of the respective liquid which flows through the feed chamber A1 onto the carrier T2.
- the capillary arrangement KA is essentially a one-dimensional lattice which, due to the surface tension of the liquid reaching the lattice openings from above, does not let the liquid through at first, but only when the liquid acts on the lattice openings with a predetermined pressure caused by gravity.
- the capillary arrangement KA has the consequence that the carrier T1 is filled with a predetermined amount of the reaction product or mixture of analyte and soluble reagent.
- reaction can be observed, for example, by coloring the support T1.
- measurement can also be carried out by means of reflectometry or by measurement of fluorescence or luminescence if a reagent or the diluent contains a fluorogenic or luminogenic component.
- a second feed chamber A2 to be filled from the outside through a filling opening F2, is connected via a second capillary K2 to a second prechamber V2, in which at least one further reagent is located on a third capillary-active carrier T3 .
- the second prechamber V2 is connected via a third capillary K3 to an empty mixing chamber Mi, which in turn is connected to the measuring chamber M3 via a fourth capillary K4.
- a nose N protrudes into the mixing chamber Mi, via which liquid which has entered the mixing chamber Mi from the third capillary K3 flows into a space Mia of the mixing chamber Mi from which the fourth capillary K4 is discharged when the mixing chamber Mi is tilted.
- the second feed chamber A2 is also connected to the measuring chamber Me via a fifth capillary K5.
- the second capillary K2 starts from a region of the second feed chamber A2 that lies approximately midway between its fill openings F2 and its bottom B opposite the fill opening F2, so that the feed chamber A2 in FIG. 2 shown position of the device is divided into an upper area A2a and a lower area A2b.
- the fifth capillary K5 starts from a point in the upper region A2a of the second feed chamber A2 which is approximately at the level of the filling opening F2.
- the capillaries K4 and K5, which lead to the measuring chamber Me containing the capillary carrier T1, are connected to the measuring chamber Me via a static capillary flow one-way valve E1 and E2, which can only flow through in the direction of this measuring chamber Me, in order to prevent that the capillaries K4 and K5 soak up the liquid which passes through them onto the carrier T1. It is particularly important that liquid which reaches the carrier T1 in the measuring chamber Me through the capillary K4 is not sucked up by the capillary K5 and that liquid which reaches the carrier T1 in the measuring chamber Me through the capillary K5 does not pass through the capillary K4 is sucked up.
- the mixing chamber Mi is also provided with a vent opening L2.
- the feed chamber A1 When using the embodiment according to FIG. 2, the feed chamber A1 is filled with sample liquid and the feed chamber A2 with diluents in the position shown in FIG. 2 (arrow I points downward).
- the feed chamber A1 empties through the capillary K1 via the carrier T2, on which the soluble reagent is located, to the carrier T1.
- the diluent in the upper region A2a of the feed chamber A2 elutes the carrier T3, on which there is another soluble reagent, into the mixing chamber Mi.
- the diluent which initially remains in the lower region A2b of the feed chamber A2 is later emptied to the carrier T1 via the capillary K5.
- the carriers T1 and T2 are washed out with the diluent, which flows in via the capillaries K4 and K5 and carries reagent which is not fixed on the carrier T1, in countercurrent to the direction of flow of the sample liquid.
- the diluent which reaches the mixing chamber Mi with the soluble reagent of T3 or through the capillary K3, flows through the nose N into the area Mia when the device is tilted into the state in which the arrow II points down, as a result of which the diluent is homogenized with the indicator reagent.
- This example describes a heterogeneous immunoassay for LH (human luteinizing hormone) according to the DASP principle.
- LH human luteinizing hormone
- Fleece A 40% linters
- Fleece B 40% polyamide
- 30% viscose 20% linters
- Fleece C 80% polyester, 20% sulfite pulp.
- the monoclonal antibodies MAK1 and MAK2 are deposited under the above-mentioned deposit numbers with the European Collection of Animal Cell Cultures, GB.
- the feed chamber A2 is filled with 450 ⁇ l 0.9% NaCl solution. The portion of this solution located in the upper region A2a of the feed chamber A2 flows down through the capillary K2, the fleece T3 and the capillary K3 into the mixing chamber Mi.
- the diluent from the lower area A2b of the feed chamber A2 flows through the capillary K5 via the one-way valve E2 into the measuring chamber Me and then into the pre-chamber V1, thereby washing out the fleeces T1 and T2.
- the liquid then passes through the capillary arrangement KA into the waste chamber Abf.
- the device is rotated so that the arrow III points downwards.
- the diluent with the indicator reagent thus flows from the mixing chamber Mi via the capillary K4 and the one-way valve E1 into the measuring chamber Me, so that the detection reaction on the fleece T1 is brought about.
- the detection reaction on the fleece T1 is observed or measured in the manner described above.
- the second prechamber V2 is in series with a third prechamber V3, in which there is an auxiliary reagent with a fourth capillary-active carrier T4 (fleece B, 6 mm ⁇ 6 mm, 0.5 mm thick, impregnated with 1.5 ⁇ Tween 20 (w / v)).
- the second feed chamber A2 is connected to the first prechamber V1 via a fourth prechamber V4, in which there is a capillary-active carrier T5.
- the second feed chamber A1 is divided into two areas A2a and A2b by a partition T.
- One area A2a is connected to the second prechamber V2 via the second capillary K2 and a one-way valve E4, and the filling opening F2 also leads into this area A2a.
- the other area A2b is connected to the fourth prechamber V4 via the fifth capillary K5.
- the feed chamber A1 is used to hold the sample liquid, the feed chamber A2 to hold the diluent.
- the diluent is divided into the areas A2a and A2b.
- the diluent flows from the feed chamber A2 through the antechambers V2 and V3 into the mixing chamber Mi.
- the nose N in FIG. 3 is only intended as protection against leakage of the liquid through the vent hole L2 and is not used for homogenization).
- the capillary K4, which leads from the mixing chamber Mi to the measuring chamber Me can optionally be interrupted by at least one further antechamber in which a capillary-active carrier is located, for example for controlling the flow velocity and for admixing inhibitors to the flow front area of those flowing from the mixing chamber Mi. Liquid.
- the receiving chamber A2 is filled with 400 ⁇ l 0.9% NaCl solution. This solution is distributed over the areas A2A and A2b of the feed chamber A2. At the same time, a sandwich complex of MAK2, analyte and conjugate is formed on the fleece T1 and its binding to the insoluble reagent via MAK2.
- the device is rotated so that the arrow IV points downward.
- the diluent from the area A2a of the feed chamber A2 elutes the fleeces T3 and T4 and reaches the mixing chamber Mi.
- the device After an incubation reaction on the fleece T1 (10 min), the device is rotated beyond the starting position shown in FIG. 3, so that the arrow V points downward.
- the diluent from the area A2b of the feed chamber A2 elutes the fleece T5 and flows through the fleece T2 and T1 into the waste chamber Abf, taking with it the reagents that are not fixed on the fleece T2 and T1.
- the liquid in the mixing chamber Mi is largely homogenized. If necessary, the homogenization can be improved by repeated tilting.
- the rotation described in the fourth step is continued, at most until the arrow VI points down, that is to say the openings F1 and F2 are at the bottom. However, it does not have to be turned so far; the flow takes place beforehand, especially during the rotation. As a result, the diluent with the indicator reagents gradually flows from the mixing chamber Mi through the capillary K4 and the one-way valve E1 into the measuring chamber Me, and the desired detection reaction takes place on the fleece T1.
- the response on the fleece T1 is measured in the manner described above.
- the device can be filled and tilted according to predetermined programs in a filling and tilting device.
- the homogenization of the liquid in the mixing chamber can also be carried out by ultrasound or gas evolution (for example CO2), in which case the device does not need to be pivoted for this.
- ultrasound or gas evolution for example CO2
- a preferred statistical capillary flow one-way valve that can be used as one-way valve E1, E2, E3, E4 has a chamber 2 in which an inflow capillary 4 and an outflow capillary 6 open.
- the wall surfaces 8 of the inflow capillary 4 enclose with the wall surfaces 10, 12, 14, 16 of the chamber 2 adjoining them angles ⁇ which are larger in their mean value than the mean angles ß which the wall surfaces 18 of the outflow capillary 6 have with the enclose adjacent wall surfaces 20, 22, 24 of the chamber 2.
- the vertices of the angles ⁇ are preferably rounded.
- the inflow capillary 4 opens in the apex region of side surfaces 14, 16 of the chamber 2 that diverge at an acute angle, and the outflow capillary 6 at right angles into a side surface 20, 22, 24 of the chamber opposite the apex region in alignment with the inflow capillary 4.
- the chamber 2 has a bottom surface 12, in which a ventilation channel 26 opens.
- Liquid flowing in through the inflow capillary 4 is not prevented by the surface tension of its front from entering the chamber 2, which is further supported by the venting channel 26, and then also enters the outflow capillary 6. If liquid tries to enter the chamber 2 from the outflow capillary 6, it is prevented from doing so by the abrupt transition of the outflow capillary 6 to the side surfaces 20, 22, 24 due to its surface tension.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Cell Biology (AREA)
- Physics & Mathematics (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Clinical Laboratory Science (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Automatic Analysis And Handling Materials Therefor (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Claims (21)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT88103194T ATE59706T1 (de) | 1987-03-02 | 1988-03-02 | Vorrichtung zur durchfuehrung einer heterogenen reaktion. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19873706718 DE3706718A1 (de) | 1987-03-02 | 1987-03-02 | Vorrichtung zur durchfuehrung einer heterogenen reaktion |
DE3706718 | 1987-03-02 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0281112A1 EP0281112A1 (fr) | 1988-09-07 |
EP0281112B1 true EP0281112B1 (fr) | 1991-01-02 |
Family
ID=6322125
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP88103194A Expired - Lifetime EP0281112B1 (fr) | 1987-03-02 | 1988-03-02 | Dispositif pour effecteur une réaction hétérogène |
Country Status (7)
Country | Link |
---|---|
US (1) | US4985204A (fr) |
EP (1) | EP0281112B1 (fr) |
JP (1) | JPH0758292B2 (fr) |
AT (1) | ATE59706T1 (fr) |
DE (2) | DE3706718A1 (fr) |
ES (1) | ES2020310B3 (fr) |
GR (1) | GR3001319T3 (fr) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4990075A (en) * | 1988-04-11 | 1991-02-05 | Miles Inc. | Reaction vessel for performing sequential analytical assays |
AU2684488A (en) | 1988-06-27 | 1990-01-04 | Carter-Wallace, Inc. | Test device and method for colored particle immunoassay |
US5104813A (en) * | 1989-04-13 | 1992-04-14 | Biotrack, Inc. | Dilution and mixing cartridge |
US5154888A (en) * | 1990-10-25 | 1992-10-13 | Eastman Kodak Company | Automatic sealing closure means for closing off a passage in a flexible cuvette |
US5288463A (en) * | 1992-10-23 | 1994-02-22 | Eastman Kodak Company | Positive flow control in an unvented container |
FR2749663B1 (fr) * | 1996-06-07 | 1998-07-31 | Bio Merieux | Carte d'analyse a usage unique comprenant un conduit d'ecoul ement de liquides |
GB9620278D0 (en) * | 1996-09-28 | 1996-11-13 | Central Research Lab Ltd | Apparatus for chemical analysis |
US6165796A (en) * | 1997-11-26 | 2000-12-26 | Beckman Coulter, Inc. | Pipettable ion detector and method |
JP4673149B2 (ja) * | 2005-06-29 | 2011-04-20 | ローム株式会社 | マイクロチップの使用方法、マイクロ流路及びマイクロチップ |
DE102011079698B4 (de) * | 2011-07-25 | 2022-08-04 | Robert Bosch Gmbh | Mikrofluidische Vorrichtung mit einer Kammer zur Lagerung einer Flüssigkeit |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3799742A (en) * | 1971-12-20 | 1974-03-26 | C Coleman | Miniaturized integrated analytical test container |
US4260687A (en) * | 1976-09-07 | 1981-04-07 | Warner-Lambert Company | Diagnostic device |
EP0049898B2 (fr) * | 1980-10-15 | 1991-08-14 | Takeda Chemical Industries, Ltd. | Procédé d'essai immunochimique et trousse de réactifs |
JPS5767858A (en) * | 1980-10-15 | 1982-04-24 | Takeda Chem Ind Ltd | Immunochemical measurement method for human chorionic gonadotropin and production of antibody |
DE3044385A1 (de) * | 1980-11-25 | 1982-06-24 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zur durchfuehrung analytischer bestimmungen und hierfuer geeignetes rotoreinsatzelement |
US4426451A (en) * | 1981-01-28 | 1984-01-17 | Eastman Kodak Company | Multi-zoned reaction vessel having pressure-actuatable control means between zones |
US4425438A (en) * | 1981-03-13 | 1984-01-10 | Bauman David S | Assay method and device |
DE3425008A1 (de) * | 1984-07-06 | 1986-02-06 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren und vorrichtung zur durchfuehrung analytischer bestimmungen |
DE3430905A1 (de) * | 1984-08-22 | 1986-02-27 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zur bestimmung einer immunologisch bindefaehigen substanz |
JPS61223561A (ja) * | 1985-01-30 | 1986-10-04 | ジエネテイツク ダイアグノステイクス コ−ポレ−シヨン | 免疫検定方法および免疫検定装置ならびに毛細管作用を有する芯 |
US4756884A (en) * | 1985-08-05 | 1988-07-12 | Biotrack, Inc. | Capillary flow device |
FR2592170B1 (fr) * | 1985-12-20 | 1988-02-05 | Guigan Jean | Procede et dispositif pour delivrer une quantite predeterminee de plasma a partir d'un echantillon de sang en vue d'analyses. |
-
1987
- 1987-03-02 DE DE19873706718 patent/DE3706718A1/de not_active Withdrawn
-
1988
- 1988-02-23 US US07/159,253 patent/US4985204A/en not_active Expired - Fee Related
- 1988-03-02 AT AT88103194T patent/ATE59706T1/de not_active IP Right Cessation
- 1988-03-02 EP EP88103194A patent/EP0281112B1/fr not_active Expired - Lifetime
- 1988-03-02 DE DE8888103194T patent/DE3861333D1/de not_active Expired - Lifetime
- 1988-03-02 JP JP63047688A patent/JPH0758292B2/ja not_active Expired - Lifetime
- 1988-03-02 ES ES88103194T patent/ES2020310B3/es not_active Expired - Lifetime
-
1991
- 1991-01-15 GR GR90401070T patent/GR3001319T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
JPH0758292B2 (ja) | 1995-06-21 |
DE3706718A1 (de) | 1988-09-15 |
EP0281112A1 (fr) | 1988-09-07 |
GR3001319T3 (en) | 1992-08-31 |
US4985204A (en) | 1991-01-15 |
ES2020310B3 (es) | 1991-08-01 |
ATE59706T1 (de) | 1991-01-15 |
DE3861333D1 (de) | 1991-02-07 |
JPS63231266A (ja) | 1988-09-27 |
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